FR2460925A1 - Procede de preparation directe d'aldehyde beta-methylthiopropionique - Google Patents
Procede de preparation directe d'aldehyde beta-methylthiopropionique Download PDFInfo
- Publication number
- FR2460925A1 FR2460925A1 FR7917827A FR7917827A FR2460925A1 FR 2460925 A1 FR2460925 A1 FR 2460925A1 FR 7917827 A FR7917827 A FR 7917827A FR 7917827 A FR7917827 A FR 7917827A FR 2460925 A1 FR2460925 A1 FR 2460925A1
- Authority
- FR
- France
- Prior art keywords
- acrolein
- stage
- beta
- water
- gaseous
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 238000000034 method Methods 0.000 title claims abstract description 20
- 150000001299 aldehydes Chemical class 0.000 title claims abstract description 16
- 238000002360 preparation method Methods 0.000 title claims abstract description 9
- HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 claims abstract description 92
- 239000000203 mixture Substances 0.000 claims abstract description 32
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 claims abstract description 30
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 29
- NIXOWILDQLNWCW-UHFFFAOYSA-N Acrylic acid Chemical compound OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims abstract description 21
- 239000007789 gas Substances 0.000 claims abstract description 20
- 239000007788 liquid Substances 0.000 claims abstract description 14
- 238000010521 absorption reaction Methods 0.000 claims abstract description 12
- 238000009833 condensation Methods 0.000 claims abstract description 11
- 230000005494 condensation Effects 0.000 claims abstract description 11
- 238000007254 oxidation reaction Methods 0.000 claims abstract description 10
- 239000007792 gaseous phase Substances 0.000 claims abstract description 8
- 230000003197 catalytic effect Effects 0.000 claims abstract description 7
- 239000007791 liquid phase Substances 0.000 claims abstract description 4
- 239000002904 solvent Substances 0.000 claims abstract description 4
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 15
- 239000008246 gaseous mixture Substances 0.000 claims description 11
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 8
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 8
- 239000012071 phase Substances 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 description 10
- 238000009834 vaporization Methods 0.000 description 9
- 230000008016 vaporization Effects 0.000 description 8
- 230000003647 oxidation Effects 0.000 description 7
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 238000004821 distillation Methods 0.000 description 5
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Natural products CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 4
- 239000011261 inert gas Substances 0.000 description 4
- -1 oxy- Chemical class 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- QYYAEQQRMTZUPJ-UHFFFAOYSA-N butanethial Chemical compound CCCC=S QYYAEQQRMTZUPJ-UHFFFAOYSA-N 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- STCOOQWBFONSKY-UHFFFAOYSA-N tributyl phosphate Chemical compound CCCCOP(=O)(OCCCC)OCCCC STCOOQWBFONSKY-UHFFFAOYSA-N 0.000 description 2
- 238000011144 upstream manufacturing Methods 0.000 description 2
- 239000002912 waste gas Substances 0.000 description 2
- GMIUDTKMYFYZEC-UHFFFAOYSA-N C(=O)C=C.CS Chemical compound C(=O)C=C.CS GMIUDTKMYFYZEC-UHFFFAOYSA-N 0.000 description 1
- FFEARJCKVFRZRR-BYPYZUCNSA-N L-methionine Chemical compound CSCC[C@H](N)C(O)=O FFEARJCKVFRZRR-BYPYZUCNSA-N 0.000 description 1
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 229910052797 bismuth Inorganic materials 0.000 description 1
- JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical compound [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 description 1
- DGAODIKUWGRDBO-UHFFFAOYSA-N butanethioic s-acid Chemical compound CCCC(O)=S DGAODIKUWGRDBO-UHFFFAOYSA-N 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 230000000295 complement effect Effects 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- 239000002826 coolant Substances 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 238000007701 flash-distillation Methods 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 229930182817 methionine Natural products 0.000 description 1
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 1
- 229910052750 molybdenum Inorganic materials 0.000 description 1
- 239000011733 molybdenum Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/78—Separation; Purification; Stabilisation; Use of additives
- C07C45/81—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
- C07C45/32—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen
- C07C45/33—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen of CHx-moieties
- C07C45/34—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen of CHx-moieties in unsaturated compounds
- C07C45/35—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen of CHx-moieties in unsaturated compounds in propene or isobutene
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/78—Separation; Purification; Stabilisation; Use of additives
- C07C45/783—Separation; Purification; Stabilisation; Use of additives by gas-liquid treatment, e.g. by gas-liquid absorption
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/78—Separation; Purification; Stabilisation; Use of additives
- C07C45/80—Separation; Purification; Stabilisation; Use of additives by liquid-liquid treatment
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/78—Separation; Purification; Stabilisation; Use of additives
- C07C45/81—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation
- C07C45/82—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation by distillation
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Crystallography & Structural Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Priority Applications (9)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7917827A FR2460925A1 (fr) | 1979-07-10 | 1979-07-10 | Procede de preparation directe d'aldehyde beta-methylthiopropionique |
| EP80400951A EP0022697B1 (fr) | 1979-07-10 | 1980-06-25 | Procédé de préparation directe d'aldéhyde de bêta-méthylthio-propionique |
| DE8080400951T DE3060131D1 (en) | 1979-07-10 | 1980-06-25 | Process for the direct preparation of beta-methylthio-propionaldehyde |
| US06/164,539 US4319047A (en) | 1979-07-10 | 1980-07-02 | Preparation of beta-methylthiopropionaldehyde |
| ES493224A ES493224A0 (es) | 1979-07-10 | 1980-07-09 | Procedimiento de preparacion directa de aldehido betametili-tiopropionico. |
| SU802948390A SU1318153A3 (ru) | 1979-07-10 | 1980-07-09 | Способ получени @ -метилтиопропионового альдегида |
| CA000355801A CA1138896A (fr) | 1979-07-10 | 1980-07-09 | Procede de preparation directe d'aldehyde beta-methylthiopropionique |
| BR8004260A BR8004260A (pt) | 1979-07-10 | 1980-07-09 | Processo de preparacao direta de aldeido beta-metiltiopropionico |
| JP9333680A JPS5653648A (en) | 1979-07-10 | 1980-07-10 | Direct manufacture of betaamethylthiopropionealdehyde |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7917827A FR2460925A1 (fr) | 1979-07-10 | 1979-07-10 | Procede de preparation directe d'aldehyde beta-methylthiopropionique |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| FR2460925A1 true FR2460925A1 (fr) | 1981-01-30 |
| FR2460925B1 FR2460925B1 (cg-RX-API-DMAC10.html) | 1981-08-14 |
Family
ID=9227700
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FR7917827A Granted FR2460925A1 (fr) | 1979-07-10 | 1979-07-10 | Procede de preparation directe d'aldehyde beta-methylthiopropionique |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US4319047A (cg-RX-API-DMAC10.html) |
| EP (1) | EP0022697B1 (cg-RX-API-DMAC10.html) |
| JP (1) | JPS5653648A (cg-RX-API-DMAC10.html) |
| BR (1) | BR8004260A (cg-RX-API-DMAC10.html) |
| CA (1) | CA1138896A (cg-RX-API-DMAC10.html) |
| DE (1) | DE3060131D1 (cg-RX-API-DMAC10.html) |
| ES (1) | ES493224A0 (cg-RX-API-DMAC10.html) |
| FR (1) | FR2460925A1 (cg-RX-API-DMAC10.html) |
| SU (1) | SU1318153A3 (cg-RX-API-DMAC10.html) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2835831A1 (fr) * | 2002-02-12 | 2003-08-15 | Aventis Animal Nutrition Sa | Procede de purification de l'acroleine |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3010429A1 (de) * | 1980-03-19 | 1981-09-24 | Bayer Ag, 5090 Leverkusen | Verfahren zur herstellung von synthesekautschuklatices, deren verwedung als haftklebstoffrohstoff bei der herstellung von haftklebemassen sowie haftklebemassen |
| US4777289A (en) * | 1986-05-08 | 1988-10-11 | Monsanto Company | Process for the preparation of alkylthioalkanoate salts |
| US4944853A (en) * | 1989-09-11 | 1990-07-31 | Pennwalt Corporation | Photochemical preparation of 3-(organothio) aldehydes |
| DE4038471A1 (de) * | 1990-12-03 | 1992-06-04 | Degussa | Verfahren zur dotierung waessriger loesungen mit acrolein in biozid wirksamer konzentration |
| US5352837A (en) * | 1993-06-08 | 1994-10-04 | Novus International, Inc. | Process for the preparation of 3-(methylthio)propanal |
| US5925794A (en) * | 1993-06-08 | 1999-07-20 | Novus International, Inc. | Process for the preparation of 3-(methylthio)propanal |
| US5905171A (en) * | 1995-06-22 | 1999-05-18 | Novus International, Inc. | Process for the preparation of 3-(methylthio)propanal |
| US5637766A (en) * | 1993-06-08 | 1997-06-10 | Novus International, Inc. | Process for the preparation of 3-(methylthio) propanal |
| KR970704681A (ko) * | 1994-07-11 | 1997-09-06 | 사이몬스 태드 더블유. 주니어 | 3-(메틸티오)프로파날의 제조 방법(process for the preparation of 3-(methylthio)propanal) |
| US5663409A (en) * | 1995-06-07 | 1997-09-02 | Novus International, Inc. | Process for the preparation of 3-(methylthio) propanal and 2-hydroxy-4-(methylthio) butanenitrile |
| US5825369A (en) * | 1996-01-16 | 1998-10-20 | International Business Machines Corporation | Compression of simple geometric models using spanning trees |
| ATE240924T1 (de) * | 1996-04-01 | 2003-06-15 | Union Carbide Chem Plastic | Verfahren zur herstellung von methylmercatopropanal |
| DE102004038053A1 (de) * | 2004-08-05 | 2006-04-27 | Degussa Ag | Verfahren zur Herstellung von 3-(Methylthio)propanal |
| DE102010064250A1 (de) | 2010-12-28 | 2012-06-28 | Evonik Degussa Gmbh | Verfahren zur Herstellung von Methylmercaptopropionaldehyd |
| CN104045590B (zh) * | 2012-04-28 | 2016-06-29 | 宁夏紫光天化蛋氨酸有限责任公司 | 甲硫醇和丙烯醛合成的粗甲硫基代丙醛的处理系统 |
| EP2679579A1 (de) * | 2012-06-27 | 2014-01-01 | Evonik Industries AG | Integriertes Verfahren zur Herstellung von Acrolein und 3-Methylmercaptopropionaldehyd |
| US20230278951A1 (en) * | 2020-07-08 | 2023-09-07 | Evonik Operations Gmbh | Process for preparing 3-methylthiopropionaldehyde |
| WO2025052079A1 (fr) | 2023-09-08 | 2025-03-13 | Adisseo France S.A.S. | Procede pour la synthese de methionine et analogues |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2626282A (en) * | 1949-10-05 | 1953-01-20 | Standard Oil Dev Co | Vapor phase production of betamethylmercaptopropionaldehyde |
| FR1520328A (fr) * | 1966-04-25 | 1968-04-05 | Sumitomo Chemical Co | Procédé de fabrication du beta-méthylmercaptopropionaldéhyde en deux étapes |
| FR1526355A (fr) * | 1966-04-30 | 1968-05-24 | Sumitomo Chemical Co | Procédé de fabrication du beta-méthylmercaptopropionaldéhyde |
| FR2314917A1 (fr) * | 1975-06-20 | 1977-01-14 | Rhone Poulenc Ind | Procede de fabrication de l'aldehyde beta-methylthiopropionique |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES357862A1 (es) * | 1967-10-13 | 1970-04-01 | Glanzstoff Ag | Procedimiento para la fabricacion de beta metilmecaptopro- pionaldehido. |
-
1979
- 1979-07-10 FR FR7917827A patent/FR2460925A1/fr active Granted
-
1980
- 1980-06-25 DE DE8080400951T patent/DE3060131D1/de not_active Expired
- 1980-06-25 EP EP80400951A patent/EP0022697B1/fr not_active Expired
- 1980-07-02 US US06/164,539 patent/US4319047A/en not_active Expired - Lifetime
- 1980-07-09 ES ES493224A patent/ES493224A0/es active Granted
- 1980-07-09 SU SU802948390A patent/SU1318153A3/ru active
- 1980-07-09 BR BR8004260A patent/BR8004260A/pt not_active IP Right Cessation
- 1980-07-09 CA CA000355801A patent/CA1138896A/fr not_active Expired
- 1980-07-10 JP JP9333680A patent/JPS5653648A/ja active Granted
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2626282A (en) * | 1949-10-05 | 1953-01-20 | Standard Oil Dev Co | Vapor phase production of betamethylmercaptopropionaldehyde |
| FR1520328A (fr) * | 1966-04-25 | 1968-04-05 | Sumitomo Chemical Co | Procédé de fabrication du beta-méthylmercaptopropionaldéhyde en deux étapes |
| FR1526355A (fr) * | 1966-04-30 | 1968-05-24 | Sumitomo Chemical Co | Procédé de fabrication du beta-méthylmercaptopropionaldéhyde |
| FR2314917A1 (fr) * | 1975-06-20 | 1977-01-14 | Rhone Poulenc Ind | Procede de fabrication de l'aldehyde beta-methylthiopropionique |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2835831A1 (fr) * | 2002-02-12 | 2003-08-15 | Aventis Animal Nutrition Sa | Procede de purification de l'acroleine |
| WO2003068721A1 (fr) * | 2002-02-12 | 2003-08-21 | Adisseo France S.A.S. | Procede de purification de l'acroleine |
| US7531066B2 (en) | 2002-02-12 | 2009-05-12 | Adisseo Ireland Ltd. | Method for the purification of acrolein |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2460925B1 (cg-RX-API-DMAC10.html) | 1981-08-14 |
| ES8104216A1 (es) | 1981-04-16 |
| DE3060131D1 (en) | 1982-02-18 |
| ES493224A0 (es) | 1981-04-16 |
| BR8004260A (pt) | 1981-01-27 |
| SU1318153A3 (ru) | 1987-06-15 |
| JPS5653648A (en) | 1981-05-13 |
| US4319047A (en) | 1982-03-09 |
| EP0022697B1 (fr) | 1981-12-30 |
| CA1138896A (fr) | 1983-01-04 |
| EP0022697A1 (fr) | 1981-01-21 |
| JPS578098B2 (cg-RX-API-DMAC10.html) | 1982-02-15 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| ST | Notification of lapse |